2-Chlorobenzoyl chloride → HCID 46843288, compound

HRID 533737Notes

Reaction equation

HRID 533737 reaction equation
[Cl:1][C:2]1[CH:14]=[N:13][C:5]2[NH:6][C:7]3[CH2:12][CH2:11][NH:10][CH2:9][C:8]=3[C:4]=2[CH:3]=1.CCN(C(C)C)C(C)C.[Cl:24][C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27](Cl)=[O:28].Cl.CCOCC>C1COCC1>[ClH:1].[Cl:24][C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27]([N:10]1[CH2:11][CH2:12][C:7]2[NH:6][C:5]3[N:13]=[CH:14][C:2]([Cl:1])=[CH:3][C:4]=3[C:8]=2[CH2:9]1)=[O:28]

Participants

6

Reactant 4

HCID 691102-Chlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 10953452Ether hydrochlorideHCID 66677239HCID 66677239, compound

Product 1

HCID 46843288HCID 46843288, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Chloro-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3′,4′-d]pyrrole (50 mg, 0.24 mmol) and DIEA (0.05 mL, 0.29 mmol) were dissolved in THF (2.00 ml). 2-Chlorobenzoyl chloride (0.04 mL, 0.29 mmol) was added dropwise, and the reaction mixture was stirred at room temperature for 1 h. The crude reaction mixture was concentrated, and converted to the HCl salt by dissolving the crude material in MeOH (2 ml) and adding 1 M HCl/ether (2 equiv). The resulting solution was refrigerated overnight. The resulting precipitate was filtered and dried under vacuum to provide 20 (47 mg, 51% yield) as a pale yellow solid. LC-MS (M+H=347, obsd.=347).

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated
  3. dissolutionby dissolving the crude material in MeOH (2 ml)
  4. waitThe resulting solution was refrigerated overnight
  5. filtrationThe resulting precipitate was filtered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-916f826f0b574fbcbc6f6b5006df2674
Source dataset
uspto-grants-2014_10
Patent number
US08853391B2

Reaction notes

Loading…